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1,2 -dimethyl-1,2-dihydroxycyclohexane + conc H2so4and heat gives you ???

3 Answers

33
Abhishek Priyam ·

pinacol-pinacolone rearrangement

1
Rohan ·

along with your answer this one has also been given .....i am not getting why a six membered ring is turning into a five membered ring even if it has an option to be a six memb. ring (your answer) .....they say that both will be in approximately same proportions

33
Abhishek Priyam ·

the point is...(when 2 adjacent-OH are present)

First -OH leaves from place where stable carbocation is formed.. then from adjacent poition one group migrates so as to form C+ at carbon having -OH..

So if methyl grp migrates then the one I gave will be formed.. and if the carbon of the ring migrates thus making it 5 membered... and the one u gave will be formed.

Also there is no much differnece between 6 and 5 membered ring as there is not too much stain in 5 mem ring.
so 6 -> 5 is also possible along with 6 -> 5

I was in a hurry so missed 1 product.

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